CALLEJON DE LA CAPILLA, a narrow, brick-paved alleyway about 200 feet long, is the nexus of cool in Old San Juan. Behind a thick wooden door is the Nuyorican Cafe, the hottest spot for live jazz and salsa; across from it is a chinchorro, or hole-in-the-wall bar, whose grittiness borders on absolute chic; and at the far end lies Calle Fortaleza, whose ultra-fancy restaurants have earned the area the ultimate sign of approbation ‚ÄĒ an acronym: SoFo.

The Frugal Traveler's standard weekend budget of $500 rarely buys entree to such trendy zones, but a free-ranging Web search netted a boutique bargain: the Nuyorican Cafe had just opened the upper floors of its bright-blue building, a former Spanish convent, as an art-filled hotel called Da House. My third-floor room ‚ÄĒ sunny but cool, with colonial-style furniture and tall, skinny windows overlooking the alley ‚ÄĒ was $80 a night. Perfect.

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